Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 23, Pages 10949-10954Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3020787
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- Propondis Foundation
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The reaction of beta-dicarbonyl phenyliodonium ylides with diphenylketene at room temperature affords mixtures of lactone and aurone derivatives. The initial electrophilic attack of the iodonium ylide on the C-beta position of the diphenylketene, followed by cyclization of the zwitterionic species, and subsequent ejection of iodobenzene, affords the lactone and aurone cycloadducts. Treatment of beta-dicarbonyl iodonium ylides with acyl chlorides yields alpha-chloroenones with good to excellent yields.
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